The present invention relates to a catalytic, one step process for readily forming polymeric material containing a multiplicity of amino nitrogen atoms therein. The subject polymeric polyamines are presently formed by complex synthetic methods as described in Offenlegungschrift No. 2,703,313 and 2,755,687 as well as U.S. Pat. Nos. 3,898,188 and 3,899,534 or by the free radical polymerization of cyclic imines such as ethyleneimine, to form the lower hydrocarbyl polyamines. The single step, catalytic process of the present invention permits the formation of a wide variety of polymeric amine/amide containing compounds in a simple, economic manner.
Catalytic alkylation of monoamines by monoolefins, carbon monoxide and hydrogen, generally referred to as catalytic aminomethylation, has been disclosed in Experiention, Vol. 5, p. 93 (1949) and Liebigs Ann. Chem., Vol. 582, p. 148 (1953). The value of the process was, however, limited by the required use of large quantities of toxic iron or nickel carbonyls as catalyst, the rapid rate of consumption of the catalyst, the slow rate of reaction, the poor yields obtained and, moreover, the reaction was found to be restricted to ethylene or propylene as the olefinic constituent.
Higher monoolefins have been reacted in the presence of other metal carbonyls to cause aminomethylation, but the reactions have been found to be non-selective and produced, at best, only moderate yields of amines. For example, U.S. Pat. Nos. 2,422,631 and 3,234,283 disclose that lower monolefins, carbon monoxide, hydrogen, and a secondary amine will form tertiary amines in low yields in the presence of cobalt hydrocarbonyl or dicobalt octocarbonyl as well as certain other cobalt compounds.
More recently, U.S. Pat. Nos. 3,513,200 and 4,096,150 have disclosed the utilization of various Group VIII metal compounds as suitable compounds to catalyze the reaction between monoamines and monomeric olefins to form low molecular weight tertiary amines.
Each of the above teachings was directed to the formation of monomeric tertiary amines. The present process is directed to the formation of highly desired polymeric polyamine/amide in a simple and economical manner.